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Total Synthesis of Nominal Cyclocinamide B and Investigation into the Identity of the Cyclocinamides.

ABSTRACT: The total synthesis of nominal cyclocinamide B, a cyclic peptide marine natural product, is reported together with an isomer of nominal cyclocinamide A. Initial attempts at the synthesis of the title compounds by inclusion of a turn inducer failed. However, direct synthesis succeeded in formation of the 14-membered cyclic peptide structure. Comparison of the data from all synthetic cyclocinamide A and B compounds with those of the natural products leads to the conclusion that the two natural products possess the same relative stereochemistry and that the true structures have not been defined.

SUBMITTER: Curzon SS

PROVIDER: S-EPMC4480797 | biostudies-other | 2015 Jun

REPOSITORIES: biostudies-other

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Total Synthesis of Nominal Cyclocinamide B and Investigation into the Identity of the Cyclocinamides.

Curzon Stephanie S SS Garcia Jessica M JM Konopelski Joseph P JP

Tetrahedron letters 20150601 23

The total synthesis of nominal cyclocinamide B, a cyclic peptide marine natural product, is reported together with an isomer of nominal cyclocinamide A. Initial attempts at the synthesis of the title compounds by inclusion of a turn inducer failed. However, direct synthesis succeeded in formation of the 14-membered cyclic peptide structure. Comparison of the data from all synthetic cyclocinamide A and B compounds with those of the natural products leads to the conclusion that the two natural pro ...[more]

PMID: 26120208

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